Casual Dresses

Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

  • Wow Factor Cutout Maxi Dress

    In this strapless maxi dress, you'll be checking yourself out in every mirror you pass! It boasts a metal square accent with a chic drape, a cutout bodice to show some skin, and a high front slit for effortless movement.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline, metal square accent, drape design
    • Padded bra cups
    • Cutout bodice, back zipper and hook-eye closure
    • High front slit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000116

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Simply Cute Tie-Front Pleated Mini Dress

    With just the snap of a finger you'll look simply cute in this tie-front pleated mini dress designed to make a statement! 

    Fit & Features

    • Woven fabric, woven lining
    • Square neckline with dual tie-front
    • Spaghetti strap ties, side zipper and hook-eye closure
    • Drop waist seam
    • Fitted silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000119

    Category Name: Casual Dresses

    Price: $7.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Striking A Pose Halter Cutout Mini Dress

    Stunning textured knit adorns this sultry bodycon mini dress with a high halter neck and cutout side accent that reveals a peak of skin!

    Fit & Features

    • Texture knit fabric, smooth stretchy knit lining
    • High halter neckline, spaghetti strap tie
    • Side cutout
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000114

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Too Hot to Handle Halter Knit Mini Dress

    This halter mini dress hugs you with a bodycon fit and a side sash that brings the drama and accentuates your curves. Pair with sandals for brunch by the beach or vacay!

    Fit & Features

    • Texture knit stretchy fabric, stretchy knit lining
    • Halter neckline with hardware trim, spaghetti strap tie
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Front wrap sash design
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000115

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Jetset Babe Tropical Print Belted Maxi Dress

    Jetset to somewhere fabulous in this tropical print maxi dress! The flattering belted waist cinches your silhouette while hidden side pockets add convenience. A sultry side slit creates movement for a trendy look.

    Fit & Features

    • Tropical multi-print, woven fabric
    • Strapless neckline
    • Belted waist
    • Hidden side pockets
    • Flowy maxi silhouette, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000112

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sent A Postcard Lace-Up Print Mini Dress

    A chic printed mini dress for your next cute trip! This dress is designed to turn heads with a lace-up back that adjusts to your perfect fit, statement puff sleeves, and a form-hugging fit that showcases your curves.

    Fit & Features

    • Printed design, woven fabric, woven lining
    • Puff short sleeves
    • Sweetheart neckline
    • Lace-up back, lower zipper and hook-eye closure
    • Form-hugging fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000113

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Forever Dreaming Strapless Cutout Ruffle Mini Dress

    Take a trip downtown or somewhere new in this strapless abstract print dress! With a cutout back, form-hugging fit, and ruffled mini hem, it's the ultimate look for summer.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Cutout back
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000110

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dinner By The Sea Tube Crochet Midi Dress

    You'll be a dreamy view in this crochet tube midi dress, enjoying a dinner by the sea. The form-hugging silhouette showcases your figure while the high side slit adds a daring touch of allure with seashell trim creates a captivating coastal-inspired look.

    Fit & Features

    • Crochet knit fabric, short knit stretchy lining
    • Strapless tube neckline
    • Form-hugging fit
    • High side slit, seashell trim
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000109

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Let's Have Some Fun Lace Bodycon Ruffle Mini Dress

    Looking for a flirty, fun vibe? Then you'll adore this lace mini dress designed with a flattering ribbon lace trim V-neckline and a bodycon fit with a ruffled hem.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Lace ribbon trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000079

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute Little Things Striped A-Line Mini Dress

    Show off your cute self in this striped mini dress for any summer occasion! The playful ruffle details add movement and feminine charm, while the flattering A-line silhouette hugs your curves in all the right places.

    Fit & Features

    • Striped print, cotton-blend lined fabric
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • A-Line silhouette, ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000106

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Meet Me in the Meadow Chiffon Floral Maxi Dress

    Easy, breezy, and made for photoshoots and parties. This strapless chiffon maxi dress with a smocked bodice and floral print gives off-carefree weekend energy with a soft, boho vibe.

    Fit & Features

    • Floral print, chiffon fabric, short woven lining
    • Strapless smocked bodice
    • Flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000107

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Island Time Tropical Floral Mesh Maxi Dress

    Get ready to be on island time in this gorg tropical floral mesh maxi dress perf for vacay. Featuring a strapless neckline and high side slit, style with heels.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large tropical floral print
    • Strapless straight neckline
    • High-cut side slit
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000102

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Major Head Turner Floral Bodycon Mini Dress

    With a sultry strut and this floral mini dress, you'll be a major head turner on vacation or at parties! 

    Fit & Features

    • Floral print, knit-lined stretchy fabric
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000103

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Cutie Denim Lace Trim Mini Dress

    This figure-flattering denim mini dress features delicate lace trim and a flirty ruffled hem that adds movement to your silhouette. The bodycon fit hugs your curves in all the right places, creating a stunning look.

    Fit & Features

    • Denim fabric, lace trim, minimal stretch
    • Sweetheart neckline, added bra cups
    • Wide shoulder straps
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000104

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Get It Girl Belted Skater Dress

    Get a bold style in this belted skater dress! The fitted waist belt and seam details accentuate your silhouette, while the pleated skirt adds movement.

    Fit & Features

    • Twill stretch fabric, stretchy knit lining
    • Strapless neckline with grommet trim
    • Back zipper and hook-eye closure
    • Seam detailing
    • Belted waist
    • Skater silhouette, pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000105

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hot In The Tropics Tropical Bodycon Mini Dress

    Walk around looking hot in this tropical bodycon mini dress while on a resort vacation or island destination! 

    Fit & Features

    • Tropical palm print, knit fabric, stretchy knit lining
    • Scoop neckline
    • Spagehtti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000101

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Uniquely Darling Strapless Pleat Skater Denim Mini Dress

    Darling and adorable, this denim mini dress brings flirtiness to any scene with a skater silhouette and pleated mini-length hem perfect for pairing with cowboy boots!

    Fit & Features

    • Denim fabric, stretchy knit shorts lining
    • Strapless sweetheart neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Pleated mini-length hem
    • Runs small

    Style Number/Barcode: 05102-000683

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: DARK, DENIM, LIGHT

    Available Size: S, M, L, XS

    Product Badge:
    • Sale
  • Definition Of Cute Off-The-Shoulder Mini Dress

    Prance around like the cutie you are in this off-the-shoulder mini dress! The playful ruffles add movement and feminine charm while the flattering form-hugging silhouette showcases your curves.

    Fit & Features

    • Woven smocked stretchy fabric
    • Ruffle off-the-shoulder neckline
    • Form-hugging silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000096

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • She's A Wildflower Strappy Back Maxi Dress

    Florals, fits, and full-on main character vibes. This floral mesh maxi dress hugs you in all the right places with a flirty strappy back and a vacay allure! 

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • V-neckline
    • Bungee strappy open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000097

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Smooth Talker Strapless Bodycon Midi Dress

    Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000724

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN-2, IVORY, PLUM

    Available Size: XS, S, M, L

  • Too Cute to Care Babydoll Mini Dress

    Low effort, high reward kind of vibe. This babydoll mini dress features a strappy cutout back and hidden pockets—aka your new throw-on-and-slay essential.

    Fit & Features

    • Poplin woven fabric
    • Square neckline
    • Spaghetti straps
    • Spaghetti strap tie-back and cutout accent
    • Hidden side pockets
    • Babydoll silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000092

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cheerful Cutie Gingham Skater Dress

    From casual plans to picnics, this cheery gingham dress will have you feeling cute all day long! This delightful dress is designed with a smocked waist for a flattering fit, a cute mini-length hem, and a flared skater silhouette.

    Fit & Features

    • Gingham print, woven fabric, stretchy knit lining
    • Sweetheart neckline with bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000093

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Head-Turning Flirt Bodycon Mini Dress

    A bodycon mini dress that makes the perfect foundation to create flirty looks!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000086

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweet On You Denim Halter Skater Dress

    Too cute to handle, too flirty to forget. This denim skater dress brings all the charm with a trendy halter neckline, heart detail at the bust, and a twirl-worthy pleated silhouette. Perfect for rooftop brunches, weekend vibes, or a little crush-worthy moment.

    Fit & Features

    • Denim fabric, minimal stretch
    • Sleeveless V-neckline, metal heart accent
    • Tie-back halter straps, partially open back
    • Hidden back zipper with hook-eye closure
    • Drop waist
    • Short pleated skater silhouette, built-in knit panty lining
    • Runs true to size

    Style Number/Barcode: 05102-000085

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free